San Juan Travel Guide

February 25, 2020

To beat the winter blues that pervade life in the Northeast, I planned a weeklong trip to San Juan in February. It was fantastic, and we found San Juan to be a welcoming, perfect place to vacation!

Recent earthquakes impacted the southern side of the Island, and though San Juan lost power for a few days, there was no other damage. The island is still recovering after the hurricane in 2017, and a wonderful way to speed up their rebuilding efforts is to visit Puerto Rico and spend some hard-earned money on local activities and food.

Traveling to Puerto Rico is relatively cheap and easy. We didn’t need a passport to get there, and most people there speak English. The currency is obviously the US dollar, which made things simple, and we found our experience to be safe and friendly.

Lodging & Transportation

After some research, we secured an Airbnb on Ashford Avenue that was across the street from Condado Beach (funnily enough, it was next to a Ben and Jerrys). This part of San Juan is extremely touristy, and locals were friendly to those visiting. It was helpful that everyone in the service industry in San Juan speaks English. Because of the proximity to the gorgeous beach and tons of restaurants, this is a popular area that I would recommend if you don’t plan on driving that much during your stay. You don’t need to go far, since everything you’ll need is within a block’s walking distance. (It’s worth noting that if you do need to drive, Ubers are readily available on the island. We got Ubers for the majority of our trip and rented a car for three days to do some exploring around the island. For a car rental, I’d recommend securing that ahead of your trip and going to Charlie’s Car Rentals, the only locally-owned car rental spot.)

I think that next time, I’d like to secure a car for the entire stay and rent an Airbnb somewhere slightly more remote. Don’t get me wrong, this was a great introduction to Puerto Rico. It’s great if you like to go out dancing or plan on shopping. But let’s be real, I was mostly there for the beach, and might prefer a quieter part of the island next time.


The food in Puerto Rico was delicious, and has influence from indigenous people, Spain, Africa, and Mexico. Plantains, mashed and whole, are often used as a side or as a base in meals.

1.) Mofongo is a Puerto Rican specialty, and it was BOMB. If you forgo this popular dish while visiting, you are seriously missing out. It’s made with fried plantains, mashed and seasoned with lots of garlic and salt. I had it with pork and a light gravy, which was great. But my favorite was the lobster mofongo we had at Waikiki (right on Ashford Avenue). It was perfect, and we paired it with fish tacos, and it was the best meal we had in Puerto Rico.

2.) We also tried blood sausage at a trendy, upscale restaurant on Condado Beach the first night we were there. Jose Enrique on Ashford had a great wine list, but I would only go there if you don’t struggle with hanger (or if you eat a snack first) because the wait was pretty long. The blood sausage, which is made with– you guessed it– animal blood, along with fats and spices, is boiled and then fried before serving. My understanding is that due to governmental regulations about transporting animal blood, it is difficult to find blood sausage in mainland US. So, we figured we’d give it a go. It was admittedly difficult to get used to its metallic, extremely rich flavor and its granular texture. I was so glad that we tried it, since I’ll try anything once (especially while traveling!).

3.) I would also recommend taking advantage of each restaurant’s catch of the day. We had tuna steaks, and a TON of fish tacos.


1.) Even if you don’t LOVE pina coladas, you have to try them here. Why? The tropical cocktail as invented here, which makes sense because the island is well known for its gigantic rum distillery. (My favorite was served at The Chapel in Old San Juan. It was not too sweet, and quite strong.) We loved getting pina coladas at the Surf Cafe on Ashford, because you could take a walk to the beach with your drink and relax near the water.

2.) Mojitos and rum and cokes were also our go-tos. Medalla is the Puerto Rican beer that is light and refreshing, and what we drank when we had had enough of the sugary cocktails.

3.) We were often served our drinks in a to-go cup, and when we asked locals about whether that was legal, they’d shrug and say, “it’s Puerto Rico!” So, we happily had open containers everywhere we went. I drank a frose as I wandered around town, and it was glorious.

Speaking of drinking, is the water safe to drink?

A lot of people ask whether the water is safe to drink, and that’s not that simple of an answer. Whenever you travel anywhere, there will be different bacteria in the water than you’re used to. So, if you have a sensitive stomach, I would recommend treating the tap water or drinking bottled water no matter where you go. The water in Puerto Rico, according to my research, is treated with the same water systems as in the continental US. The water tasted totally fine, and I felt normal after drinking it. You should note that Puerto Rico does not have a system for recycling plastic water bottles, and this definitely impacted my decision to drink tap water as much as possible.


1.) San Juan was so appealing to us because of its many beautiful beaches that are easily accessible. Our two favorites that were easily within walking distance of our Ashford apartment were Playita del Condado and Condado Playa. Condado Beach (pictured below) is close to everything and is super fun. When we went, there was a long stretch of the beach that had rainbow flags and music playing. (Side note, from my perspective, San Juan appeared to be a gay-friendly tourist destination.) It’s one big party there, and people will walk by with food carts or you can rent a chair with waiter service for food and drinks. At 5pm or so, the beach gets much quieter and it’s a great spot for some mellow people-watching. We loved going during this time of day and then wandering around looking for a good dinner spot after. The beach itself is not very swim-friendly, as the waves are massive and a little scary. This is more of a sun-bathing, drinking type of beach. It’s great for people watching. A ton of models come here and we noticed many swimsuit ads being shot.

2.) Playita del Condado is a smaller beach that is farther down Ashford Avenue. It is about a 10 minute walk from Condado Beach. It appealed to me mostly because a reef shelters the swimming area from massive waves, so the water is serene and crystal clear. It is fun too, with a food truck selling drinks. Swimming here was relaxing and fun.

3.) My favorite beach in San Juan was Balneario El Escrambron. A cheap Uber ride or a 25-ish minute walk from Condado, this beach is gorgeous for snorkeling. We brought our snorkel gear and explored, seeing many varieties of fish around a small reef. Again, because this reef sheltered the swimming area from rough waves, it was fun for swimming. The water here was the clearest, most turquoise water I’ve ever seen. There are iguanas sun bathing on the rocks, and we saw some parrots in the palm trees.

4.) If you get the chance to explore other beaches on the island, I would highly recommend checking out Luquillo and Fajardo. Luqillo was my favorite beach in Puerto Rico. It is the perfect, most Instagram-able spot with fine white sand and blue water. Locals go here along with tourists, and the vibe is family-friendly and just plain friendly. There’s a food shack with VERY cheap beer, and we were quite content to spend two days on this beach.


1.) Though not in San Juan, I would be remiss if I did not mention El Yunque. If you have access to a car, drive about 45 minutes east to El Yunque National Rainforest. I never thought I would go to a rainforest, and this one is the only one part of the National Park system in the US. It looks and feels like a jungle. It is easy to drive through, with many pull-offs along the way with hiking trails leading to waterfalls or beautiful sights. I would recommend taking a cell phone photo of the map at the entrance of the park, and then stopping along the way at the pull-offs you want to visit. The Yokahu Tower is a must! Plus, the rainforest is close to Luquillo Beach, which in my opinion is a must-see.

2.) A five minute Uber ride will take you to Old San Juan, which was my favorite place to visit (so much so that we spent three days here). You can just walk around aimlessly for hours, dipping into a bar for a quick drink, shopping, and listening to all of the street music.

Pictured below are views from our visit to Castillo San Cristóbal, the Spanish fort built almost 500 years ago. The sights on the top of level of the fort were gorgeous, and it was very cool to explore the dungeons below where prisoners and rebels against the Spanish crown were kept in the humid dark.

3.) Darsenas Square was bustling with local artists selling merchandise. There was a lot of food carts and music to enjoy.

4.) You’ll notice while exploring Old San Juan that flags are everywhere. The most striking of them all to me was the black and white flag pictured below (photo 1) on San Jose Street, which was spray painted black at night by a group of women whose artist collective was later known as “La Puerta.” Pretty freaking cool, and you should go see it.

In a nutshell, what you should know is that the black and white stripes symbolize resistance to the Puerto Rico Oversight, Management, and Economic Stability Act passed under President Obama’s administration. Puerto Ricans were largely dissatisfied with this plan, since it meant that the people in charge of implementing extreme changes in Puerto Rico’s economic structure (including a suggested decrease of the minimum wage) were not Puerto Rican. The black and white flag has been adopted by many people as a symbol of anti-colonization.

5.) You’ll still see the huge original Puerto Rican flag on Calle de la Fortaleza (there are no longer umbrellas there, which we found out upon arrival). The massive flag is one of the most Instagrammed spots on the island.

I loved the center photo, also taken on this street. I didn’t know what the numbers spray painted to his right meant, but after some research, Arlo discovered that they represent the number of those killed in Hurricane Maria.

I would recommend exploring more of Calle de Fortaleza. There’s a small park near the chapel with amazing views. The restaurants here are great, and you can find some really cool souvenir shops. The best souvenir I bought was on this street in an unmarked store. We bought a vejigante mask to take home, which is easily the coolest souvenir in our home collection.

I learned so much about Puerto Rican culture, and how resilient its people are despite the colonization by the US government that has left it massively in debt and unsustainable. Many locals we talked to are hoping for statehood to end their taxation without representation and to give them the same rights that states have. They also discussed the need for less imports and more farming as a means for Puerto Ricans to be self sustaining. Despite not having the right to vote, we found that many young people on the island are politically energized, hoping for real and impactful change. I fell in love with Puerto Rico, and I want it to be a sustainable place for people to live and thrive. You can’t go wrong visiting here, since you’ll boost their economy (if you shop local!) and have a great time doing so.

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